I finished up my freshman year of college a few months ago. This story is about me and my roommate, who started off with a long distance girlfriend. I had a media center pc with two monitors: the one on my desk, and the plasma on the wall. With only basic cable in the dorms, I was using a slingbox to get all of our digital channels. Because John only had a netbook, he always used my computer for the video chats he had with his girlfriend so that he could see her on the big screen... and the calls were pretty frequent. He always bragged about how he had convinced his girlfriend to give him camera shows of her masturbating, but refused to ever let me sit in and watch.
After weeks of begging with the 'how's she gonna know if I'm off camera,' he finally gave in. The one rule was that if he signaled me to leave, I would do it... so I agreed. I took a seat at my computer, john on the couch in front of the plasma, and we connected to her on skype. After no time at all, sure enough, there was his girl getting herself off on the camera with a rubber dildo. I was hard before she even got naked. I looked over at John and he had his hand in his shorts so I was sure he was enduring the same... then she asked it: 'are you hard??' He said he was but immediately she said 'well get those pants off and let me see. I want to watch you cum.' In a bit of a panic, John stood up and fiddled with the belt buckle for a second as he kicked stuff in my direction to signal me to get out. I got up to leave, but instantly it dawned on us that there was no way for me to do so from my corner without crossing into the field of the camera's view, and it would be awfully suspicious to reach up and block the camera. With john now standing, his face was out of the shot and he gave me this 'God hates me, I knew this was a bad idea' look, but we were both aware of the decision he was now facing in those mere seconds. He could tell the truth: that he violated her trust and privacy and let his buddy watch her ram a giant rubber dong up her pussy. Or he could pretend like nothing was wrong, whip it out, and jerk off for her. In hindsight, there were certainly a few other alternatives like ripping the camera from the tv or me pulling the connection, but in those 10 seconds John said all he could think about were the recent fights they'd had and how likely the truth would have ended their relationship. He chose to whip it out. For all I know, he wanted to do it in front of me. If I had a dick that big I'd certainly be proud of it. We'd already seen each other naked a dozen times, never erect, though he had shown me a clip of them having sex before. Nevertheless, with almost identical schedules, it was rare to have all the 'private time' we wanted... we both jerked off regularly under the covers in the dark, but nothing was ever said.
Anyways, he mouthed the words 'tell anyone and I'll kill you' I laughed a bit, then did the only thing that came to mind: I was horny as hell, and with all this masturbating going on around me, it seemed pretty silly to just sit there with a raging hardon in my shorts. Clearly John was past worrying about me seeing him, so it was pretty stupid for me to just sit there. I pulled my shorts off, stood up and started jerking off too. When I sat back down, John's dick was pretty much right in front of my eye-line to the TV, so I was getting a pretty good look at that monster while watching his girlfriend. After a few minutes though, I found myself fixated on his cock and not her... which would have been pretty awkward if, however, John wasn't staring at my cock instead of his girlfriend. If she could see which way he was looking, I'm sure she'd be more pissed off that he was fixated on his masturbating roommate over his masturbating girlfriend. When I was staring at his cock in the forground, I had the TV with his girlfriend in the background as my scapegoat... John had no such excuse for staring at my cock as I stroked away. He liked watching me. When John was getting close, he told his girl he was about to cum and sat back down. He erupted like a volcano shooting his load all over his chest. It was that sight that sent me over the edge, and I had a ridiculously powerful orgasm myself. She actually commented on how hard he came, proud of herself for getting him that turned on. At that point he was still laying back, completely spent, when she says 'what if your roommate walked in right now.' He said something like I'm sure he jerks off too, then jokingly said 'I think this is his sock' which he proceeded to use to wipe the massive amount of cum off of himself and then threw towards me. I cleaned myself up but neither of us put our clothes back on. When he finally ended the call, he was the first to speak, saying something along the lines of 'Well I guess we don't have to worry about finding private time to jerk off anymore.' I was relieved it didnt make things awkward, and thrilled that he was interested in repeating the experience. We joked around a bit and were just lounging around in the nude for a while watching tv. We jerked off a few more times that night, then pretty regularly for the rest of the year. For the most part it remained just jerking off together... all the freakin time actually, we usually even waited for the other to get home before taking care of business. Later on in the year, it evolved into giving each other handjobs and a bit more experimentation, but for the most part we were just jerk off buds. We now share an apartment off campus, but with a third roommate, opportunities have been scarce.